The Boston Sunday Sports Section
The Jaylen Brown Dilemma
The Celtics would appear to be at a fork in the road moment in terms of keeping or trading Jaylen Brown. Their failed pursuit of Giannis has raised questions about whether the relationship with Brown can be repaired or whether they will now trade him, with many credible sources believing the latter to be the likely outcome.
This being New England, though, it is less a fork in the road and more like a rotary with multiple exits heading in different directions, shaping the franchise’s direction for years to come. The report from Shams Charania that Boston has asked ‘in some cases’ for as many as four first-round picks is a very high bar. Still, this was a shocker because trading Brown for picks would be taking a step backwards and make 2027 and even 2028 the ‘gap years’ that 2026 was supposed to be.
The good news is the Celtics have Brad Stevens driving the car, and I would even trust him at one of those crazy Boston-area ‘squares’ where five roads all come together.
Let’s run through the potential exit paths. In This Week in Basketball, Tyler Rourke will go deeper into what some of these options might look like in terms of which players they would add.
1) Run It Back
Run it back with Brown and Tatum and reshape the roster around them.
2) Reload
Trade Brown for players to try to win now.
3) Rebuild
Trade Brown for a win-later package — draft picks, young players, or a combination of the two.
The Two Real Trade Paths, Side by Side
Illustrative examples only — not reported trade packages.
4) Circling the Rotary
Stevens is just floating Brown to see if he can get a ‘godfather’ offer. He is basically driving the car around the rotary, but planning to come back to the start.
Look, kids — Big Ben, Parliament.
This ultimately comes down to whether Stevens thinks they can win a championship in the next two seasons with Tatum, Brown, and a reshaped roster. The Knicks essentially ran it back with the same group this season and won a title. Stevens added KP and Jrue to the Jays in 2024 and won a title, so it would not be unprecedented.
His actions so far, both by offering Brown plus picks for Giannis and, even more so, by continuing to engage in trade talks with Brown, would seem to indicate that he does not believe he has the right core with Tatum and Brown to win another title. Sure, he has praised Brown publicly and said how important he has been to the team, but actions speak louder than words, and what else is he going to say?
I don’t like Option 3. It is like the old game show ‘Let’s Make a Deal’ where you could end up with a new car in four years, or you could end up with a goat, and not the G.O.A.T variety.
Would they still make the playoffs with Tatum and a young core? Very likely. Would they go anywhere once they did? Likely not for several years.
The NBA, more than any other league, is a king-of-the-hill league where teams need to go up the mountain, getting pushed down for several years before finally reaching the top. There have been seven different champions in the past eight years, with only the previously battle-tested and champion Warriors winning more than one. They all had several playoff stumbles before reaching the top.
I don’t see the point in Option 4, and it doesn’t seem to be the way Stevens operates.
I would have traded Brown for Giannis because, when healthy, Giannis can still play at an MVP level. With Giannis off the board, I would pick Option 1 and at least give it another year with Tatum fully healthy. Brown is a professional who understands it is a business, and he likely uses this as motivation rather than sulking.
It would appear, though, that Stevens is planning to take a different exit.
The countdown of the USA’s Top Ten Sports Moments leading up to our nation’s 250th anniversary will continue with Number 6. These are the moments that have us ‘Proud to be an American’ and chanting U-S-A, U-S-A.
See below for the prior editions. Number 10 was part of a Boston Daily Sports Recap; Numbers 9 through 1 are standalone pieces.
What Do They Buy?
Most of the talk around the Red Sox selling at the trade deadline has focused on the pieces they would sell. Aroldis Chapman and Sonny Gray are the obvious pieces.
Wilson Contreras and Garrett Whitlock will likely be dangled for a steep price. Jarren Duran’s value is certainly less than it was prior to the season, but he could still fetch a good return and may excel with a change in scenery.
If anybody wants spare parts like IKF, Monasterio, Connor Wong, or Justin Slaten, get what you can for them. If someone wants Trevor Story, Brayan Bello, or Marcelo Mayer, trade them and then rule that person out when you look for your replacement for Craig Breslow.
And if anyone wants Breslow, do the ‘I’ll have what she’s having’ from When Harry Met Sally.
The more important question, though, is what do they buy?
There are three answers:
1) Established power hitters at positions of need and several years of control.
2) Pitching – particularly high-octane, potential high-leverage bullpen arms.
3) Power-hitting prospects with high upside.
Power at Positions of Need
Power is Boston’s most glaring need. It was before the season, and the need has only gotten more acute.
Even if there is a season next year, there is no equivalent power bat on the free agent market this offseason to Kyle Schwarber and Pete Alonso.
The Red Sox need two full-bladder batters. What I mean by that is when you were at Fenway, and Papi or Manny or Mookie or Raffy was up, you waited until their at-bats were over before you headed for the restroom.
This year, you head to the restroom when the Red Sox come to the plate so you don’t have to watch.
Heading into Saturday’s game, the Red Sox are tied with Tampa for last in baseball with 69 home runs. They are 27th in average exit velocity at 87.3 mph. They hit the seventh most ground balls of any team in baseball.
They are in good shape in the outfield with Abreu, Rafaela, and Anthony.
The primary positions of need are Catcher, Second Base, Third Base, and DH. That assumes they don’t trade Contreras and Franklin Arias becomes your shortstop.
Do you revisit Ketel Marte? Would the Astros Yordan Alvarez be your DH? Could you trade for Byron Buxton and have him DH to help save wear and tear? He is an outfielder, but do you call the Mets about Juan Soto, given their struggles? Could you pry Adley Rutschman away from Baltimore since they have Samuel Basallo? Could you trade the A’s Gray and some young pitching and pry away Shea Langeliers, since it will be hard for them to attract free-agent pitchers to Sacramento and Las Vegas?
Some of these will take a lot more than Gray and Chapman, perhaps high-end pitching prospects like Anthony Eyanson, but they literally need to swing for the fences because there is very little power in this year’s free agent class (Randy Aronzarena and Seiya Suziki top the class and both are outfielders). I would listen to offers on Connelly Early as well.
The only minor leaguer I would put off limits is Franklin Arias.
The Red Sox were said to be looking for right-handed power. All else being equal, sure, but the left-handed slugging David Ortiz seemed to do perfectly fine at Fenway.
Pitching
Yes, they are in good shape in the rotation with Crochet, Suarez, Tolle, and Early all locked up for at least the next four years. But you almost have to assume one of those four will be out at any given time, just given the rate of pitcher injuries. That leaves a couple of holes in the rotation if you trade Gray, and you can never have too much pitching.
I would go for high-risk, high-reward type arms who have an exceptional fastball and one breaking or off-speed pitch, but need to develop one or two more pitches to be successful Major League starters. The reason why is that those pitchers either develop those pitches, like Tolle has made progress on this year, or they become your high-leverage relievers.
Prospects
Some high upside, power-hitting prospects who have been part of deadline deals include:
Yordan Álvarez and Junior Caminero are the prime examples here of low-minors lottery tickets the Astros and Rays struck it big on. But the better path for the Red Sox is high-minors power hitters who may not be Top 100 prospects but are organizational top-ten prospects, blocked, or undervalued by their current organization, in the mold of Randy Arozarena or Adolis Garcia when they were with St. Louis.
The Blue Jays, for example, just called up third baseman Sean Keys, who has 21 home runs in the minors but may be blocked at his position. Lazaro Montes strikes out a ton but has light tower power and could DH.
These are, by nature, no sure things, but they need to take some swings.
John Sarianides argues the organization mishandled its prized infield prospect — rushing, shuffling, and ultimately running him into an injury. A pointed counterweight to the ‘trust the process’ line.
Rob Bradford on a night that actually felt good — Payton Tolle near-perfect against the Yankees, a Contreras dust-up, and a reminder that even a lost season has its moments.
Boston Bets on Upside in the Draft
The Boston Celtics rarely find themselves in a position to draft a prospect with significant upside. Because of the organization’s sustained success over the past decade, Boston has consistently selected near the end of the first round, where role players like Hugo González and Jordan Walsh are often the safest options.
Still, Celtics President of Basketball Operations Brad Stevens has made a habit of finding players fans can get excited about. Whether it was Robert Williams III’s athleticism and rim protection, Payton Pritchard’s scoring ability, or Hugo González’s defensive energy, Boston has consistently found value late in the draft.
This year, however, the Celtics may have landed something different.
With the 27th overall pick, Boston selected Chris Cenac Jr., a 6-foot-11, 240-pound big man out of the University of Houston. Once ranked as the No. 7 recruit in his high school class, Cenac brings size, rebounding, and athleticism to the frontcourt. At just 19 years old, he also possesses intriguing upside as a floor-spacing big who relentlessly attacks the glass. In his lone season at Houston, Cenac averaged 9.5 points, 7.9 rebounds, and 0.7 assists per game.
Boston’s Ability to Develop Centers
One of the Celtics’ greatest strengths in recent years has been their ability to maximize the talents of their centers. This year being a great example, taking a rotation of nobodies and turning them into serviceable players.
Neemias Queta spent much of his early career with the Sacramento Kings organization, primarily developing in the G League, where he earned All-Defensive First Team honors and finished as an MVP runner-up. Despite his talent, he struggled to carve out a consistent role at the NBA level. Since arriving in Boston, the Celtics have put him in positions to succeed and have helped him become a valuable contributor.
Robert Williams entered the league as an athletic shot blocker and rebounder, but his game expanded significantly during his time in Boston. Beyond protecting the rim, Williams developed into an excellent screen setter, an above-average passer for a center, and a player with impressive touch around the basket.
Even Luke Kornet, who struggled to establish himself before joining the Celtics, found his footing in Boston. What once looked like a fringe NBA career turned into one of the league’s most reliable backup center roles.
That track record should excite Celtics fans when it comes to Cenac. While still a raw prospect, Cenac flashed plenty of potential during his time at Houston. His athleticism, motor, and willingness to chase rebounds and loose balls make him an intriguing developmental project for a franchise that has consistently gotten the most out of its big men.
What to Expect Right Away
Cenac’s biggest strengths entering the NBA are his physicality and activity on the offensive glass. Those traits alone address a need within Boston’s center rotation, but his long-term upside is what makes him particularly intriguing.
Early on, Cenac may not see consistent minutes. Even in a limited role, however, his offensive flashes could surprise fans. He has a smooth mid-range jumper that he is comfortable taking off the catch, and his per-36-minute numbers have the potential to be eye-catching.
Expect him to be a player Boston turns to when the team needs an energy boost or a spark off the bench.
Who Is Boston’s Second-Round Pick?
The Celtics added another impressive athlete in the second round by selecting Dillon Mitchell, a high-flying 6-foot-7 wing who should provide plenty of highlight-reel moments when given opportunities.
Mitchell spent four years in college and played for three different programs before finishing his career at St. John’s, where he averaged 8.3 points, 7.0 rebounds, and 3.0 assists per game.
Like Cenac, Mitchell projects as a versatile defender capable of switching across multiple positions. His biggest limitation is his offensive game, particularly his shooting. After four years of college basketball, most of his scoring still comes around the basket.
Even so, Mitchell possesses traits that translate to the NBA. His frame, athleticism, and defensive versatility give him a pathway to becoming a valuable role player and carving out a lengthy professional career.
The pick-heavy path made concrete: Portland, flush with young talent and draft capital, is the kind of suitor that fits Exit 3 in the Editor’s Take — a rebuild-style return for Brown.
And the win-now path: the Duren-type return that fits Exit 2 — trading Brown for an established inside presence rather than a pile of picks.
The Bruins Take a Chance
The two primary tenants of TD Garden might be going in surprisingly opposite directions.
The contending Celtics are floating the possibility of trading a star in Jaylen Brown for a haul of draft picks.
The still rebuilding Bruins went the opposite route Friday night, trading picks for pucks in nets. It is a strong signal that Don Sweeney and company think the Bruins are a team on the rise after last season’s surprise playoff appearance.
Minutes before the first round began in Buffalo Friday night, Boston traded its first-round pick, No. 23 overall, along with Florida’s 2028 first-round pick (top-10 protected) to the Utah Mammoth for right wing J.J. Peterka.
Boston is wagering that a change of scenery, Shipping Up to Boston replacing the Mormon Tabernacle Choir, and a bigger role will push those numbers back up.
And if it doesn’t, at least he can get a beer after the game. Knowing nothing else about the situation, a German in Salt Lake City sounds like a mismatch.
Peterka is a 24-year-old German winger and a proven top-six scorer. He put up 25 goals and 47 points in 82 games for Utah last season, and the year before that, with Buffalo, he set a career high with 68 points. He is signed through 2030 at a $7.7 million cap hit, so the Bruins are not renting him.
On the surface, trading two first-round picks for one player sounds steep. But the price is less daunting than it looks. A pick at No. 23 is a first-rounder in name, but NHL draft value falls off sharply right around there. Success rates drop considerably from the mid-20s into the second round, and forwards taken that late hit at a much lower rate than lottery picks.
The player Boston would have drafted at No. 23 was unlikely to help a contending roster for years, if at all. The 2028 pick they sent, originally Florida’s, projects to land late in the first round as well.
That is what makes this trade significant beyond just acquiring Peterka. It is a clear win-now signal. The Bruins chose a known 24-year-old NHL scorer over two draft picks. Don Sweeney and the front office are telling you they intend to compete now.
The catch is that one winger does not make Boston a contender. A 47-point scorer is a real addition, but the Bruins still have holes, such as a top-six center and a right-shot defenseman. The same analysts who liked the Peterka deal were quick to point out that those needs remain, and the free-agent market that opens July 1 is thin.
There is some risk in the bet itself, too. Peterka was a ‘Mammoth’ disappointment in Utah as his production slipped from 68 points to 47 in his lone season there.
For a team that has spent the past year somewhere between contender and question mark, the Peterka trade is the clearest indication yet of which direction the Bruins think they are heading. Now they have to prove the rest of the roster can follow.
Nick Goss breaks down the full cost and fit — the two first-rounders out, Peterka’s contract and production in, and what the deal says about Boston’s timeline.
Who Boston actually walked away with after dealing the first-rounder — a rundown of the Day 2 selections and where they fit in the system.
Phil Perry’s rankings bump McDaniels up seven spots to No. 4 — a vote of confidence in the brain trust around Drake Maye heading into a pivotal Year 3.
Perry’s top five: Maye, Campbell, Williams, A.J. Brown, and Christian Gonzalez — a useful map of where this roster’s leverage really sits.
Thanks for reading Issue 10 of The Boston Sunday Sports Section. If you’re not yet a subscriber, we’d love to have you. And if you enjoyed it, please share it with your fellow Boston sports fans.